It's no great surprise that the autodidact Nevile Gwynne was on the judging panel – the poor man has been the victim of myriad Restoration-themed spelling errors. However, you may have discerned a slight political subtext when you learned that the panel also included the free school evangelist Toby Young and the rightwing journalist Harry Mount. That subtext has been made a little less "sub" now that the award has been handed to the academics who wrote a letter of protest about Michael Gove's education policies. It's a letter that was, said the judges, studded with solecisms. According to Toby Young: "The 100 educators have inadvertently made an argument for precisely the sort of formal education the letter is opposing."

However, one can approve of the award without liking its political intent. Pointing out the linguistic infelicities of others is practically a national sport. Everyone loves Lynne Truss. Our self-esteem is under near constant assault from magazines telling us how fit we could be or how nicely decorated other people's homes are. If we can snatch a brief taste of superiority with a chuckle at our local greengrocer's haphazard apostrophe placement, where's the harm?

I'm certainly prone to live-subediting what I hear on radio or television. It's just mild hothousing when I correct my daughter's grammar, but it would be pretty annoying if I were to chide adults for writing "should of". Telling strangers in a pub that they should say "she was sitting" rather than "she was sat" would probably result in a glassing.

I am, though, sometimes guilty of passive-aggressively echoing someone else's sentiments with datives or subjunctives slotted in where appropriate. I can't help it. For happy-go-lucky pedants like me that's the highlight of any dinner party.

I know better than to play that game with my father-in-law though. He was educated 20 years before me, when grammar schools actually taught grammar as a formal structure, over which language was then draped. By the time I came along, that notion had been abandoned and I was taught the grammar only of foreign languages.

I learned to reverse-engineer the rules of English from those of French and German. And I picked up some useful stuff about split infinitives from reading Clive James's reviews of Star Trek in the Observer.

Noam Chomsky theorised that grammar is genetic, that we have an implicit understanding of the way language is put together that predates any formally learned structure. He first floated that idea in the 1950s. Coincidentally, soon afterwards, spoken English began to throw off the rigid corsetry of strict grammar, and started strolling the streets of the media in its demotic pyjamas.

Our recent veneration of footballers has been another pernicious influence on language. I believe that the area of the brain responsible for the correct use of adverbs is immediately adjacent to the part devoted to accurately tracking a ball in flight. It's rare to have both of these sectors running at full power.

Where speech goes then the written word soon follows. The effect has been accelerated by online communication, where 20-word Facebook updates and 1,000-word blogposts alike are presented to a potential audience of millions without the slightest attention from a subeditor. Indeed, some of the less scrupulous online news outfits have effectively outsourced subbing to their readers. Grammatical howlers, and even errors of fact, are gleefully reported in the comment sections beneath news stories. The worst offences are later corrected in the text, and the helpful corrections are spirited out of existence. Still, the commenters have felt that fleeting sense of superiority, so perhaps it's a fair exchange.

Does any of it matter? As long as we more or less understand each other, can we dispense with the fusty old rules and ablatively freestyle away from the old grammar into a groovy, post-syntactic future?

I don't think so.

Right now unprecedented numbers of non-native English speakers are living in Britain. They have learned their English from textbooks, not from birth as I did. They'll probably never think in English.

Most of us know the stress of translating on-the-fly when we're on holiday. Imagine feeling that pressure for the rest of your life. Removing the stabilisers of grammar from the bike of language isn't clever – it's cruel.

Furthermore, at some point in the future, voice command is likely to overtake keyboard input as our primary method of controlling computers. It's sensible to remove ambiguity from language as much we can before we reach that point. And if that means everybody has to improve their diction too, then so much the better.

The bad grammar award, with its typo-bestrewn press release, may be intended as a joke, but in a future where literal-minded computers will control every aspect of our existence, that joke might just save our lives.